CN1151187C - 主链含双键的共聚型共轭聚合物及其制备方法和用途 - Google Patents
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Abstract
本发明公开了一类主链含双键的共聚型共轭聚合物及其制备方法和用途。这种聚合物是由芳杂环、稠环化合物或其衍生物与二芳基乙烯类化合物直接氧化偶联而得到,制备方法简单,成本低,可批量制备结构多样、功能更全的多种共轭聚合物,这种聚合物可作为发光材料用于制作发光二极管、电致发光器件、光致发光器件及其它光电转换器件和产品。
Description
技术领域
本发明涉及共聚型共轭聚合物及其制备方法和用途,具体地说是主链含双键的共聚型共轭聚合物及其制备方法和用途,这些聚合物可用于制造发光二极管及其它光电转换器件。
背景技术
有机发光二极管中用聚合物作发光层或电荷传输层,常用的聚合物有聚对苯撑乙烯(PPV)及其衍生物,聚对苯撑(PPP)及其衍生物,聚乙烯咔唑(PVC2),聚苯乙烯等,其中以主链由芳基与乙烯基交替组成聚合物
聚芳撑乙烯)最为普遍。但要在主链上引入乙烯基常常需要特殊的单体或复杂的反应(Wessling,R.A.et al,USP3 401152,USP3 706677),因而这些化合物制备困难,成本高,制备规模小。此外,为了制备有较强电子传输能力的聚合物,需要在主链中引入恶二唑结构;而引入喹啉结构则可提高材料的稳定性,延长器件寿命。这些结构的引入都使合成工作变得复杂,难以得到批量产品。用氧化偶联法合成聚对苯撑及其衍生物的方法最为简单,但目前还只合成了聚对苯、聚萘等数种聚合物,仅传输空穴,发光效率低,难以适应制备高性能器件的要求。
发明内容
本发明的目的是提供一种主链含双键的共聚型共轭聚合物及其制备方法和用途,该共聚型共轭聚合物的制备不需要额外列入官能团而直以芳杂环作聚合单体,且能在主链中引入多种芳杂环和双键形成类似聚芳撑乙烯的结构,因而具有优良的发光性能,可以批量生产并满足器件对发光材料的不同要求。
为实现一述目的,本发明所采用的技术方案如下:
一种根据本发明,共聚型共轭聚合物的通式如下:
式中,Ar代表含一个或多个苯环的胺类或烷烃、芳杂环或稠环化合物及其衍生物,如咔唑,三苯胺,三苯甲烷、喹啉、奈、蒽等;
代表二芳基乙烯类化合物或其衍生物,如二苯乙烯、二噻吩乙烯、二萘乙烯或二吡咯乙烯等;m,n为1,2,…自然数。
上述共聚型共轭聚合物的制备方法:
本发明的共聚型共轭聚合物是由上述
所代表的单体直接氧化偶联共聚所得,具体方法如下:
在惰性气氛保护催化剂作用下,在适当的溶剂中,两种单体于-20-+40℃下反应2-40小时后,分离除去无机物,在醇类溶剂中沉淀聚合物后通过洗涤除去催化剂和未反应完的单体,洗涤剂为水或醇。
根据本发明的技术方案,所述的催化剂为A1Cl3、FeCl3、TiCl4、CuCl2、或它们的混合物;
根据本发明的技术方案,所述的溶剂为硝基苯或氯芳、二氯甲烷、四氯化碳等卤代烃;
本发明所得产物能溶于普通溶剂,吸收波长为200-700纳米,发光波长为300-800纳米,分解温度>250℃,可用于制造发光二极管、其它电致发光器件、光致发光器件及其它光电转换器件和产品。
在反应中以芳杂环上的活性氢为反应官能团,无须如一般聚合反应那样在单体上引入双官能团,省去了制备单体的复杂反应步骤,使得发光材料的制备步骤简化,成本大大降低,也可以在苯环、杂原子上引入烷基,烷氧基等基团,增强共轭聚合物的溶解及加工性能,制备出结构多样、功能更全的多种共轭聚合物,以满足实际应用对材料的不同要求。
本发明所提出的共聚型共轭聚合物的制备方法利用二芳基乙烯为单体,由于乙烯基不参与反应,因而很方便地在聚合物主链中导入双键,形成类似聚芳撑乙烯的结构,克服了制备困难的缺点。还可通过选择有不同功能的化合物进行二元、三元甚至多元共聚合,可以方便地在聚合物主链中引入多种复杂结构,批量制备结构多样、功能更全的多种共轭聚合物,因而比目前的聚芳撑乙烯的诸多制备方法具有更多的灵活性。
本发明的另一个优点是利用大体积分子与体积较小的分子共聚,能克服芳香大环间的位阻效应,使不能聚合反应的稠环分子发生氧化偶联聚合,大大扩充了氧化偶联反应的应用范围,能制备出多种结构的共轭聚合物。例如烷基咔唑很难进行均聚合,与小分子如对苯二烷基醚,二苯乙烯就能发生共聚反应,通过简单的氧化偶联反应生成发光聚合物。
所制备出的共聚型共轭聚合物可以通过共聚合引入多种结构,实现多种功能,满足实际应用对材料的不同要求。例如可以把具有电子传输和空穴传输能力的芳烃分子共聚合,得到的聚合物能同时传输空穴和电子,使发光效率大大提高;在分子中引入芳杂环以增强材料的抗老化性,增加材料的稳定性;引入相容剂以改善发光层与电极间的界面状况,延长器件寿命。
具体实施方式
以下结合具体的实施例对本发明的技术方案作进一步的说明:
实施例1:
0.40克庚基咔唑,0.54克反式1,2-二苯乙烯,加到250毫升三口烧瓶中,加入新蒸氯仿75毫升,搅拌使其溶解,加入2.93克干燥无水氯化铁,在干燥氮气保护下室温反应24小时。停止反应,漏斗上抽滤除去氯化铁,用氯仿洗涤滤渣数次,合并滤液。将滤液倾入120毫升甲醇中,搅拌2小时后沉淀,收集产物,并用甲醇洗涤,60℃干燥,得0.57克棕色粉末。特性粘度0.3-10.0g·dL-1。经红外,紫外,核磁共振谱证明其为共聚物,荧光光谱证明其最大发射强度位于430纳米处,为兰光发射材料。
实施例2
将3.7克三苯胺与2.7克反式1,2-二苯乙烯溶于200毫升氯仿中,得亮绿色溶液。另在干燥保护下,在500毫升反应瓶中加入300毫升氯仿和10克无水三氯化铁,并将前述的三苯胺与二苯乙烯溶液滴入,常温搅拌24小时,停止反应。过滤,滤液稍浓缩至约200毫升,冷却后加入约500毫升甲醇,搅拌1小时,抽滤,得到黑色片状沉淀。在60℃下烘干,得到产物1.9克,经红外、元素分析、核磁鉴定为共聚物,荧光分析其发射峰值约430纳米,为蓝光发射材料。
实施例3
0.32克9,9-二己基芴和0.30克1,2-(2,5二噻吩)乙烯溶于30毫升四氯化碳中,并将溶液置于滴液漏斗中。该漏斗接在三口反应瓶上,该反应瓶还装有冷凝水管和导气管。在干燥氮气或氩气保护下,向该反应瓶中加入0.35克无水三氯化铁和0.3克无水二氯化铜及20毫升四氯化碳,搅拌下滴加二己基芴和二噻吩乙烯混合物,室温下继续搅拌30小时。停止搅拌、过滤,将滤液倾入150毫升甲醇中,搅拌1小时,过滤,滤渣用石油醚和甲醇洗涤数次,干燥,得产物0.29克。产物在氯仿和四氢呋喃中有较好溶解性,经元素分析、红外、紫外、磁共振证明为共聚物,发光波长最强处约460纳米,为兰光发射材料。
Claims (4)
2.权利要求1中所述的主链含双键的共聚型共轭聚合物的制备方法,
其特征在于:它是将选自庚基咔唑、二己基芴、三苯胺之一的单体
Ar与选自二苯基乙烯或二噻吩乙烯的单体
直接氧化偶
联聚合而得到共聚型共轭聚合物。
3.根据权利要求2中所述的方法,其特征在于:氧化偶联是在惰性气
氛保护及催化剂作用下,在适当的溶剂中进行,单体Ar和单体于-20-40℃下反应2-40小时后,分离除去无机物,在醇类溶剂中沉淀聚合物后通过洗涤除去催化剂和未反应完的单体,洗涤剂为水或醇,所述的催化剂为AlCl3、FeCl3、TiCl4、CuCl2或它们的混合物;所述的溶剂为硝基苯或氯仿、二氯甲烷、四氯甲烷。
4.权利要求1所述的主链含双键的共聚型共轭聚合物用于制造发光二极管、电致发光器件及其光电转换器件或产品。
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KR101073283B1 (ko) | 2003-06-05 | 2011-10-12 | 막스뎀 인코포레이티드 | 일렉트로루미네센스 재료의 정제방법, 일렉트로루미네센스 재료 및 일렉트로루미네센스 소자 |
CN100387641C (zh) * | 2003-06-05 | 2008-05-14 | 日立化成工业株式会社 | 电致发光材料的精制方法、电致发光材料以及电致发光元件 |
US7507351B2 (en) | 2003-06-05 | 2009-03-24 | Hitachi Chemical Co., Ltd. | Method for purifying electroluminescent material, electroluminescent material and electroluminescent device |
US8075943B2 (en) | 2005-12-27 | 2011-12-13 | Hitachi Chemical Co., Ltd. | Purification process for organic electronics material |
CN101613477B (zh) * | 2009-07-16 | 2012-08-08 | 浙江工业大学 | 主链含萘衍生物的共轭聚合物发光材料的制备方法 |
US8697895B2 (en) | 2009-08-05 | 2014-04-15 | Dow Global Technologies, Llc | Process for producing an oxirane |
US8524926B2 (en) | 2009-11-19 | 2013-09-03 | Dow Global Technologies Llc | Epoxidation of an olefin |
CN108997518A (zh) * | 2018-08-07 | 2018-12-14 | 福建师范大学 | 一种蓝色发光的聚苯乙烯的合成方法 |
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